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| Names | |
|---|---|
| Preferred IUPAC name Oxindole | |
| Systematic IUPAC name 1H-indol-2(3H)-one | |
| Identifiers | |
3D model (JSmol) | |
| 114692 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.000.390  |
| EC Number |
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Gmelin Reference | 637057 |
| KEGG | |
| MeSH | Oxindole |
PubChem CID | |
| RTECS number |
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| UNII | |
CompTox Dashboard (EPA) | |
InChI
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SMILES
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| Properties | |
Chemical formula | C8H7NO |
| Molar mass | 133.150 g·mol−1 |
| Melting point | 128 °C (262 °F; 401 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Oxindole (2-indolone) is an aromatic heterocyclic organic compound. It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing ring. Oxindole is a modified indoline with a substituted carbonyl at the second position of the 5-member indoline ring.
Oxindole is a tryptophan derivative and in human biology is formed by gut bacteria ("normal flora"). It is normally metabolized and detoxified from the body by the liver. In excess, it can cause sedation, muscle weakness, hypotension, and coma. Patients with hepatic encephalopathy have been recorded to have elevated serum oxindole levels.[1]
Related aromatic compounds
- Indoline
- Indole
- Indene
- Benzofuran
- Isoindoline
- Carboline
- Isatin
- Methylindole
- Carbazole
- Pyrrole
- Skatole
- Benzene
References
- ^ Riggio, Oliviero; Mannaioni, Guido; Ridola, Lorenzo; Angeloni, Stefania; Merli, Manuela; Carlà, Vincenzo; Salvatori, Filippo Maria; Moroni, Flavio (2 February 2010). "Peripheral and Splanchnic Indole and Oxindole Levels in Cirrhotic Patients: A Study on the Pathophysiology of Hepatic Encephalopathy". The American Journal of Gastroenterology. 105 (6): 1374–1381. doi:10.1038/ajg.2009.738. PMID 20125128. S2CID 20633097.